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Well-defined Poly(lactic acid)s Containing Poly(ethylene glycol) Side-chains.

ABSTRACT: Poly(ethylene glycol) (PEG) side-chain functionalized lactide analogues have been synthesized in four steps from commercially available L-lactide. The key step in the synthesis is the 1,3-dipolar cycloaddition between PEG-azides and a highly strained spirolactide-heptene monomer, which proceeds in high conversions. The PEG-grafted lactides analogues were polymerized via ring-opening polymerization using triazacyclodecene as organocatalyst to give well-defined tri- and hepta-(ethylene glycol)-poly(lactide)s (PLA) with molecular weights above 10 kDa and polydispersity indices between 1.6 and 2.1. PEG-poly(lactide) (PLA) with PEG chain M(n) 2000 was also prepared but GPC analysis showed a bimodal profile indicating the presence of starting macromonomer. Cell adhesion assays were performed using MC3T3 E-1 osteoblast-like cells demonstrating that PEG-containing PLA reduces cell adhesion significantly when compared to unfunctionalized PLA.

SUBMITTER: Castillo JA

PROVIDER: S-EPMC3263433 | biostudies-literature | 2012

REPOSITORIES: biostudies-literature

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Well-defined Poly(lactic acid)s Containing Poly(ethylene glycol) Side-chains.

Castillo José A JA Borchmann Dorothee E DE Cheng Amy Y AY Wang Yufeng Y Hu Chunhua C García Andrés J AJ Weck Marcus M

Macromolecules 20120101 1

Poly(ethylene glycol) (PEG) side-chain functionalized lactide analogues have been synthesized in four steps from commercially available L-lactide. The key step in the synthesis is the 1,3-dipolar cycloaddition between PEG-azides and a highly strained spirolactide-heptene monomer, which proceeds in high conversions. The PEG-grafted lactides analogues were polymerized via ring-opening polymerization using triazacyclodecene as organocatalyst to give well-defined tri- and hepta-(ethylene glycol)-pol ...[more]

PMID: 22279245

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